Dear Prudence,
I’m a 31-year-old male and consider myself to be a borderline sociopath. I view this as a neural development disorder where many people fall along a spectrum, not something to be “treated” or changed. I have a strong “logical morality” and do not wish harm to anyone, but I do come first and don’t commonly feel guilt or remorse. This seems to work in most areas of my life, but dating is a problem. By all recognizable accounts I am easygoing, successful, charming, and normal. However, I do not feel love the way I imagine many people do. My love for someone peaks around the two-month mark in the relationship and I can feel that way for nearly anyone who meets my dating criteria. But I have been the “love of their life” for many women, who form incredibly deep bonds and end up devastated after they realize our relationship will not progress and it ends for seemingly no reason. In some of these relationships I have even been entirely up front that I simply don’t “feel” the way most people do and they have not been deterred. So, what am I to do? I don’t enjoy hurting others, but I do enjoy when others care for me. Do I just continue this pattern throughout life, enjoying each relationship for what it is and knowing that if the woman gets her heart broken she will eventually get over it and go on to better relationships? Or is that callous and morally demanding of a better approach?

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—Not a “Feeler”

Dear Not,
Thank you for a peek inside the brain of “that guy.” The guy who discards women like they’re stained clothing, yet always has someone new to try. The guy who makes no explicit promises, who even sometimes admits he’s not like other people, but who behaves as if the deepening feelings are mutual. The guy who when told by the woman he is seeing that she loves him, realizes it’s time to move on—and when questioned about the breakup asserts it’s simply not his fault if she misunderstood his attentions. Let’s take your borderline sociopath diagnosis at face value, and accept that you don’t want treatment, and frankly for major personality disorders there isn’t that much to offer. Because you don’t want to hurt others, you indeed are on the benign end of this spectrum, a kind of Mr. Spock. (At the malignant end are those who revel in causing pain, personified by serial killer Ted Bundy.) It even makes a certain evolutionary sense that a small number of people like you serve a useful societal function. You are the hyper-rational creature who can make decisions without the clouding lens of human feeling. It also makes sense that you have your pick of partners. Sailing through life with confidence and élan is attractive.

You do acknowledge that you have your own emotional needs, and that they are not about having reciprocal feeling but about the gratification of being adored. So having applied your ample analytic skills to your situation, your question is what you should do about it. You’re right that you could go through life as a perpetual bachelor, breaking hearts and eventually making your friends queasy about fixing you up, but morality requires that you don’t knowingly continue this hurtful pattern. So stop making vague declarations about your lack of feelings. Be explicit at the beginning that you have never been in—and don't care to start now—a relationship that lasted more than a few months. State that marriage is not for you. Say you offer a good time in the short term. Some women will take this as a challenge, but they do so at their own risk. But surely, there are also some female Spocks out there, and if you get tired of the endless chase, look for a woman who is as cool and unromantic as you. You two would likely make a formidable if unsettling team, moving forward together like a pair of beautiful sharks.

—Prudie

Dear Prudence,
I’m having an existential dilemma. I’ll be turning 30 this year, and while most of my friends got to spend their college years and a few “back in the nest” years having great adventures (road-tripping across the U.S., traveling to foreign countries, etc.) I did not. I went to college on a scholarship but had to work to support my ailing father, who passed away when I was 21. I had to take responsibility for his finances, dig him out of medical debt, and pay for his dozen prescriptions, which no doubt informs my current need to be financially stable. My parents divorced when I was young, and my mother offered no support during this time and refused to let me move back in with her after my dad died. (Our relationship is fine now.) I have a corporate office job that is unfulfilling and for which I’m underpaid, but I know I should be grateful just to have a job. My dream is to work in animal rescue, like my husband, but that work is notoriously low-paying. I keep fantasizing about quitting my job, taking some time to have a grand adventure, and finding a job I love instead of one where I am wishing the day away. I am tired of living for the future—building up a 401(k) and investing in my home’s property value—when the future is never certain. After all, I could die at 54 like my father without getting to retire and enjoy the fruits of my labor. So what do I do?

—Stuck

Dear Stuck,
Unlike many in your generation, you are already reaping the rewards of your hard work and frugality. You are making a retirement nest egg and building equity in your home. You don’t have student loans! Believe me, many of those who pursued their wanderlust are now lusting after financial stability and employment. You by nature sound conservative and cautious. These are valuable qualities that you can apply to designing a future that has more excitement and fulfillment—without leaving you broke and homeless. First of all, you have a job, but you need a career. Given what you were able to accomplish for your father while still a college student, you need to reassess how you’re using your considerable management skills. Sure, you’d love to take care of stray animals, but you can volunteer at a shelter on the weekends. During the week you need something more remunerative and challenging. It sounds as if you’d make an excellent certified financial planner! (Here’s a brief aptitude test to help get you thinking about your strengths.) Contact your college’s career counseling office for advice on getting unstuck at work. Once you have focused on ways to improve your professional life, explore what to can do to have more fun. Maybe you and your husband can take short road trips over long weekends. Maybe you save for a two-week blowout at an exotic locale. You have taken on responsibilities beyond your years for most of your life. Now it’s time to stop fantasizing about what could be, and start making it happen.

Dear Prudence,
Our daughter is graduating from high school and we are planning a large celebration. We are inviting many people, not just family but friends from near and far, classmates, and teachers. Our daughter has been active in sports and has had a teammate who’s year younger. The girls have been on travel teams together and we have gotten close to the family. The moms have become good friends. The problem is the daughter. She has been a challenge and more so of late. She’s very loud and frequently inappropriate and abrasive with her words and behavior, to the point of making all around her uncomfortable. While our daughter would love to have the mom come to the party, she’s had it with the daughter and is afraid she will ruin her celebration. Not inviting them at all will certainly be perceived as a slight. What’s a parent to do?

—Perplexed Dad

Dear Dad,
You invite both the mother and the daughter. It’s true your daughter doesn’t have to be friends with a girl she doesn’t like, but it is also not acceptable to exclude her from a function at which her lack of invitation is a billboard-sized snub. Take this opportunity to talk to your daughter about having empathy for someone who’s troubled and doesn’t fit in. But also tell your daughter that you and her mother will keep an eye on “Callie,” and if she starts to act up you will intervene. That could mean anything from interrupting an outburst by asking her to help you in the kitchen, to having a quiet word with Callie’s mother that the girl needs the teenage equivalent of a time out. But if you are seriously concerned this one girl can ruin a big party, Callie may have problems beyond the usual scope of hormones and adolescent obnoxiousness. Since you say the two mothers are close, if your wife thinks this girl is spinning out of control, she should have a private conversation with the other mother, in which she can say how much she cares for Callie and that she’s concerned the girl seems to be in distress. Let’s hope the mother heeds the warning and gets her daughter some help.

—Prudie

Dear Prudence,
I had a rough couple of years and really let my home go. I didn’t clean anything, didn’t even do the dishes or take out the trash. I stopped letting anyone in my apartment. About six months ago I decided enough is enough. I started a new job and made new friends. I researched long and hard to find someone to hire to help clean my home and she did an excellent job. Then a strange coincidence happened. A friend of mine is a Facebook friend of hers. My friend called today to warn me that my cleaning lady took pictures of my disgusting home and posted them on Facebook and God knows where else. I feel ashamed and violated, exposed and betrayed. How do I approach this without completely losing my mind with her?

—Hoarder in Recovery

Dear Recovery,
Let’s for a second put aside the grotesquely unprofessional behavior of your housekeeper, and congratulate you for recognizing the abyss into which you’d sunk and addressing it so thoroughly. This should be inspiring to others who have dealt with despair. But as excellent as your housekeeper’s skills may be, she has a disastrous lack of respect for her customers. So your first step should be to call her out. You have her number, so let her know you’ve been alerted to the photos, that you were understandably shocked, and that you request she take them down immediately from Facebook and anywhere else. I’m betting that will do it. Consider that very few people will have seen her posts, and once they’re no longer up, you should stop worrying. If she refuses, then report her to Facebook. Even though she’s not going to make a second appearance at your apartment, do find a more trustworthy replacement so that you can continue to enjoy your clean start.

“Kissing Siblings: My brother and I were always close, but now we’ve started making out.”
“Molesting Dentist: My son’s onetime dentist acted suspiciously, and now he’s been arrested for child porn. What should I do?”
“Say What?: My white boyfriend just called someone the N-word.”
“She’s Keeping It: My friend got pregnant by a jerk. Can she keep the baby a secret from him?”